NPASS Compound

Natural Product: NPC509712

Natural Product ID	NPC509712
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(hexanoyloxy)-3-(tetradecanoyloxy)propyl tetradecanoate
IUPAC Name	(2-hexanoyloxy-3-tetradecanoyloxy-propyl) tetradecanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 113112 0 0 0 0 0 0 0 0999 V2000 13.4361 3.9395 1.1468 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1036 4.6063 0.8728 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0312 3.5729 0.6014 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8432 2.6396 1.7993 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7500 1.6619 1.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4359 0.6621 2.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3732 -0.2909 1.9542 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0692 0.3709 1.5985 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0934 -0.6725 1.1016 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7466 -0.0569 0.7357 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8831 0.9909 -0.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6447 1.6528 -0.7893 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 0.8656 -1.5339 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1127 -0.2831 -0.8173 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3518 -1.4450 -1.2740 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3663 -0.1481 0.3086 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8005 -1.1938 1.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2428 -2.0013 0.3592 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7901 -2.9977 1.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8984 -3.6532 0.8776 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0891 -3.0275 0.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1674 -1.7915 0.7443 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2088 -3.8287 -0.0354 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4144 -2.9748 -0.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9328 -2.4982 1.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1961 -1.6280 0.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8066 -0.4229 0.1446 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0206 0.4490 -0.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5985 0.8925 1.2206 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8032 1.7617 0.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4319 2.9789 0.2027 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6711 3.8638 -0.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1816 5.0594 -0.8283 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3207 6.0151 -1.1370 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8964 6.4613 0.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1189 -2.6779 -0.8037 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5053 -2.5194 -2.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4567 -1.7160 -2.1515 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0835 -3.2693 -3.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8727 -4.3508 -2.8044 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3242 -5.1209 -4.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2823 -6.2108 -3.5841 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5023 -7.1094 -2.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4421 3.5147 2.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5520 3.1309 0.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2277 4.6846 1.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1915 5.2592 -0.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7930 5.1942 1.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2882 2.9233 -0.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0341 4.0632 0.4653 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7698 2.1354 2.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4924 3.2558 2.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1686 1.1205 0.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8836 2.2921 1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3155 0.0779 2.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0329 1.1998 3.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2229 -1.0943 2.7340 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7427 -0.7728 1.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6441 0.8174 2.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2910 1.0995 0.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5613 -1.1920 0.2509 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9375 -1.4257 1.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3518 0.3753 1.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 -0.8943 0.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4100 0.5565 -1.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5358 1.8348 0.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2022 2.1711 0.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9689 2.5310 -1.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1005 0.5459 -2.5404 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7827 1.5500 -1.8294 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3768 -0.7215 1.9768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5904 -1.8825 1.4295 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0755 -1.3205 0.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0014 -3.7709 1.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0636 -2.4990 2.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4176 -4.6902 0.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8111 -4.2181 -1.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0619 -2.0751 -0.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1793 -3.5277 -0.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2778 -3.3456 1.7637 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2129 -1.8527 1.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0289 -2.1894 0.5218 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3931 -1.2747 2.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4602 -0.6908 -0.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9895 0.1369 0.6568 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7793 1.2974 -0.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7940 -0.1442 -0.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8716 1.5047 1.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8559 0.0442 1.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5393 1.1244 0.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2347 2.1063 1.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7493 3.5887 0.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9769 2.8398 -0.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0426 4.1329 0.9712 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4316 3.2737 -0.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3983 5.5557 -0.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7175 4.6613 -1.7571 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8909 6.8612 -1.7007 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0581 5.4664 -1.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9765 7.5599 0.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8609 5.9406 0.3518 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2213 6.1596 1.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3683 -2.5537 -3.9670 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9905 -3.7039 -3.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3070 -4.9942 -2.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7205 -3.8764 -2.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7686 -4.4205 -4.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4387 -5.6013 -4.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5926 -6.7714 -4.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1364 -5.7511 -3.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9141 -8.1364 -2.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6191 -6.6753 -1.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4157 -7.0766 -2.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 18 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 0 13 70 1 0 17 71 1 0 17 72 1 0 18 73 1 0 19 74 1 0 19 75 1 0 23 76 1 0 23 77 1 0 24 78 1 0 24 79 1 0 25 80 1 0 25 81 1 0 26 82 1 0 26 83 1 0 27 84 1 0 27 85 1 0 28 86 1 0 28 87 1 0 29 88 1 0 29 89 1 0 30 90 1 0 30 91 1 0 31 92 1 0 31 93 1 0 32 94 1 0 32 95 1 0 33 96 1 0 33 97 1 0 34 98 1 0 34 99 1 0 35100 1 0 35101 1 0 35102 1 0 39103 1 0 39104 1 0 40105 1 0 40106 1 0 41107 1 0 41108 1 0 42109 1 0 42110 1 0 43111 1 0 43112 1 0 43113 1 0 M END

Standard InCHIKey	UFWKHGDIQGGVAN-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C37H70O6/c1-4-7-10-12-14-16-18-20-22-24-27-29-35(38)41-32-34(43-37(40)31-26-9-6-3)33-42-36(39)30-28-25-23-21-19-17-15-13-11-8-5-2/h34H,4-33H2,1-3H3
SMILES	CCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.52	Volume:	693.34 ? Van der Waals volume.
Dense:	0.881	LogP:	3.835 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.197 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.247 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	36.0	Rigid Bonds:	3.0
TPSA:	78.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.042	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.311	Fsp³:	0.919
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.597	Fluc inhibitor:	0.28 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.013 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.952	Promiscuous compounds:	0.342

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.134	MDCK Permeability:	-4.832
Pgp-inhibitor:	0.001	Pgp-substrate:	0.375
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.958
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.998
Plasma Protein Binding (PPB):	100.358%	Volume Distribution (VD):	1.363
Fu:	0.54% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.092
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.694
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.134	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.073 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.605

Half-life (T1/2):

1.969

ADMET: Toxicity

hERG Blockers:	0.788	hERG Blockers (10um):	0.912
Human Hepatotoxicity (H-HT):	0.421	Drug-induced Liver Injury (DILI):	0.516
AMES Toxicity:	0.302	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.118	Skin Sensitization:	1.0
Carcinogencity:	0.853	Eye Corrosion:	0.136
Eye Irritation:	0.499	Respiratory Toxicity:	0.564
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.212
Hematotoxicity:	0.125	Drug-induced Nephrotoxicity:	0.82
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.947	Hek293 Cytotoxicity:	0.235
BCF:	-0.749 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.33 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.797 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.758 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC509712 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	25236
0.1-0.2	22159
0.2-0.3	2169
0.3-0.4	180
0.4-0.5	64
0.5-0.6	30
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55678
0.7647	Intermediate Similarity	NPC602940
0.75	Intermediate Similarity	NPC54925
0.6429	Remote Similarity	NPC224700
0.6429	Remote Similarity	NPC320663
0.6207	Remote Similarity	NPC47363
0.6207	Remote Similarity	NPC250028
0.6207	Remote Similarity	NPC236579
0.6207	Remote Similarity	NPC80234
0.6207	Remote Similarity	NPC287231
0.6207	Remote Similarity	NPC203531
0.6207	Remote Similarity	NPC256163
0.6207	Remote Similarity	NPC40597
0.587	Remote Similarity	NPC488690
0.5806	Remote Similarity	NPC603863
0.5625	Remote Similarity	NPC603612
0.561	Remote Similarity	NPC48218
0.561	Remote Similarity	NPC141481
0.561	Remote Similarity	NPC464342
0.5588	Remote Similarity	NPC488257
0.5588	Remote Similarity	NPC469937
0.5588	Remote Similarity	NPC94699
0.5588	Remote Similarity	NPC320588
0.5588	Remote Similarity	NPC53463
0.5517	Remote Similarity	NPC53541
0.551	Remote Similarity	NPC83839
0.5455	Remote Similarity	NPC149299
0.5455	Remote Similarity	NPC310746
0.5294	Remote Similarity	NPC26253
0.5294	Remote Similarity	NPC489083
0.5294	Remote Similarity	NPC23155
0.5227	Remote Similarity	NPC473559
0.5227	Remote Similarity	NPC324981
0.5192	Remote Similarity	NPC488693
0.5192	Remote Similarity	NPC488689
0.5161	Remote Similarity	NPC63182
0.5161	Remote Similarity	NPC145045
0.5161	Remote Similarity	NPC52700
0.5152	Remote Similarity	NPC80396
0.5152	Remote Similarity	NPC154642
0.5152	Remote Similarity	NPC600941
0.5143	Remote Similarity	NPC128061
0.5094	Remote Similarity	NPC331437

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC509712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6706
0.1-0.2	2279
0.2-0.3	139
0.3-0.4	16
0.4-0.5	3
0.5-0.6	2
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6125	Phase 4
0.6571	Remote Similarity	NPD3730	Pre-clinical
0.6429	Remote Similarity	NPD8278	Phase 4
0.6207	Remote Similarity	NPD2699	Pre-clinical
0.6	Remote Similarity	NPD8277	Approved
0.575	Remote Similarity	NPD3728	Approved
0.551	Remote Similarity	NPD8304	Clinical (unspecified phase)

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data